Chuck's Conquest
by pheasant14
Summary: Chuck has decided to take over both St. Jude's and Constance by seducing the girl's of Constance and using to find dirt on other students. Multiple pairings, a lot of smut. Set in season 1.
1. Chapter 1

Chuck Bass stood atop the Empire State Building looking down on NYC, a wicked grin spread across his face. He had formed a plan, a plan that would allow him to take St Jude's and Constance for his own, dethroning Queen B and the rest of her cronies and making sure that he had everything and, more importantly, everyone he wanted. He would slowly take Blair's cronies away from her until finally she had nothing.


	2. Chapter 2

Phase 1: Little J

Chuck was well aware of how much Jenny Humphrey wanted to be part of the 'in' crowd. The beginning of the plan would be the most difficult. If he couldn't build up his allies then he could quickly go from controlling both schools, to socially dead and while he didn't care as much about social standing as Blair or the other Constance girls, he was well aware of how a collapse in social standing may influence his father's opinion of him. His decision to begin with Jenny was extremely calculated. He was sure she would be easy to manipulate.

Jenny had only walked 100 metres out of the Constance gates before a black limo pulled up alongside her. The window rolled down to reveal Chuck, the man that had once attempted to rape her. "Hello little J, would you like Arthur to drive you to your little home? I'm sure if you got into a limo it would be all over Gossip Girl and people might start thinking you're somebody." Jenny didn't say a word but got into the limo, Chuck eyed her in her dress and licked his lips, soon all of this would be his. "I'm going to be throwing a nice party in my suite in a few days, all you need is to go to this party and soon you will be one of them, another big shot at Constance." The idea of it was alluring for Jenny. All she wanted was to be liked, to be popular. This party seemed to be the perfect chance for her to become popular, but Chuck wasn't finished "All that would be required for you to get an invitation would be to have a little fun with me, to be popped by Chuck Bass, like so many other Constance students before you. How does that sound?"

Jenny shuddered in revulsion, her dignity or popularity, in the end she had to choose between the two, "With my support you would be able to overthrow Blair and become the Queen of Constance, all you have to do is work with me a little."

Jenny nodded tentatively. She'd had a few boyfriends in middle school and had done everything up to sex, but this would be her first time. She moved her mouth over to his in a pointless attempt to be seductive, Chuck sneered, "Stop screwing around and let me see your tits." He roughly ripped the top of her dress and grabbed her bra, tearing it to shreds. He smiled and took out his 9-inch cock, "Suck it slut". Jenny looked at him and obeyed, using her hands to massage his balls while keeping the head in her mouth. She swirled her tongue around his dick, causing Chuck to moan in pleasure. "Take in more, you fucking whore, take the whole dick." Chuck said roughly as he began to thrust his dick in her mouth. Jenny's throat began to make a gargling sound as she choked around Chuck's dick but she loved the feel of it, giving head had always been one of her favourite past times, she remembered that time in the taxi with Nate during Blair's birthday party, how she had made him cum in her throat. As Jenny began to get used to Chuck's enormous penis, she pulled her panties off from under her dress and began to finger herself, moaning into Chuck's penis. She began to feel his dick throb and pulled off so he came all over her face and boobs. Smiling, she looked Chuck dead in the eye and wiped the cum off of her breasts and face with her hand before licking it.

"Fuck me Chuck, I want it." Jenny was going to make sure that Chuck enjoyed this, even if she lost all her dignity in the process. If Chuck enjoyed it, he would be more likely to keep his side of the bargain. Jenny positioned herself so she was looking out the windscreen of the limo and he ass was in the air so Chuck could take her from behind. Chuck lifted up the back of Jenny's dress and slowly began to force his penis in, Jenny felt like she was being split open. When Chuck reached her hymen he launched a vicious thrust destroying the small flap of skin and causing a small trickle of blood to go down her leg. As he began to pump in and out of Jenny her pain turned to pleasure at being filled up, and she was moaning. He pumped in and out of her and all Jenny could feel was the ecstasy of sex, she didn't care about pride or dignity anymore, all she wanted was sex. Chuck continuously ploughed, giving Jenny orgasm after orgasm.

After Jenny's fourth orgasm, Chuck leaned forward into her long blonde hair and began to massage her breasts while still pumping into her. When Chuck finally launched his load deep inside her Jenny let out a cry of pleasure. As he pulled out a slowly deflating penis, Chuck watched his seed slowly leek out of Jenny's vagina, while Jenny lay on the backseat of his limo, exhausted from the amount of pleasure her body had experienced. While she lay over the backseat he wiped the excess semen on her breasts and when he finally got hard again, came in her hair.

When Jenny awoke she found herself lying in her bed with her boobs and vagina still exposed with semen on her face, boobs and in her hair. On the dressing table next to her was an invitation to a party with a USB drive on the back of it, on it was written:

_Jenny Humphrey, you are requested on the top floor of The Palace Hotel._

_C. Bass._

As Chuck was in the back of his limo thinking about his conquest, he looked up at the camera set up to film the back seats of his limo a smiled. Jenny was his.


End file.
